All Episodes

August 5, 2024 30 mins

Jonathan Small has been chronicling the failures and successes of people for most of his career. From doing his first interview (with George Carlin) to his sharing dating tips as “Jake” for Glamour magazine to his stint as an editor at Entrepreneur magazine to his experience interviewing hundreds of writers on his Write About Now podcast, Small has been a fly-on-the-wall for many failure-to-success stories.

Now he’s released a book made up of the origin stories of some of the writers he’s interviewed, which I’m proud to say Legacy Launch Pad has published. With insights from as wide a variety of people as Killers of the Flower Moon author David Grann to 90s fashion queen Betsey Johnson, Write About Now reveals the failures and successes of a succession of greats.

In this interview we talked about the main qualities successful people have in common, our shared experience starting our careers working at parenting magazines and why many companies would be far better off sharing the struggles of the founder, among many other topics.

For more info, go to www.failyourway.com.

Mark as Played

Advertise With Us

Popular Podcasts

Stuff You Should Know
The Joe Rogan Experience

The Joe Rogan Experience

The official podcast of comedian Joe Rogan.

Two Guys, Five Rings: Matt, Bowen & The Olympics

Two Guys, Five Rings: Matt, Bowen & The Olympics

Two Guys (Bowen Yang and Matt Rogers). Five Rings (you know, from the Olympics logo). One essential podcast for the 2026 Milan-Cortina Winter Olympics. Bowen Yang (SNL, Wicked) and Matt Rogers (Palm Royale, No Good Deed) of Las Culturistas are back for a second season of Two Guys, Five Rings, a collaboration with NBC Sports and iHeartRadio. In this 15-episode event, Bowen and Matt discuss the top storylines, obsess over Italian culture, and find out what really goes on in the Olympic Village.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.